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Title: Transition Metal‐Free sp 3 −sp 3 Carbon‐Carbon Coupling between Benzylboronic Esters and Alkyl Bromides
Abstract

A transition metal‐free coupling reaction of benzylboronic esters and alkyl halides has been developed. Both alkyl bromides and alkyl iodides were found to be competent substrates with the nucleophilic boronate intermediate generated from the combination of benzylboronic ester and an alkyllithium. Good chemoselectivity was observed for the reaction with the alkyl bromide in substrates with a second electrophile present. Both secondary and tertiary benzylboronic esters were effective nucleophiles in the reaction with primary alkyl halides. Mechanistic observations are consistent with a radical mechanism.

 
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NSF-PAR ID:
10238402
Author(s) / Creator(s):
 ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
European Journal of Organic Chemistry
Volume:
2021
Issue:
19
ISSN:
1434-193X
Page Range / eLocation ID:
p. 2782-2784
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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